diff --git a/packages/esm-shim/src/utils.ts b/packages/esm-shim/src/utils.ts
index ddf14be5d..a1bb1d504 100644
--- a/packages/esm-shim/src/utils.ts
+++ b/packages/esm-shim/src/utils.ts
@@ -13,24 +13,27 @@ function matchAllPolyfill(input: string, pattern: string | RegExp): RegExpMatchA
     return [];
   }
 
+  let idx = 0;
   for (let i = 0; i < result.length; i++) {
-    output.push(result[i].match(new RegExp(pattern)) || []);
+    const match: RegExpMatchArray = [result[i]];
+    match.index = idx;
+    idx += result[i].length;
+    output.push(match);
   }
   return output;
 }
 
-export function matchAll(regex: RegExp, input: string, addition: Record<string, any>) {
-  const matches = [];
-  for (const match of matchAllPolyfill(input, regex)) {
-    matches.push({
-      ...addition,
-      ...match.groups,
-      code: match[0],
-      start: match.index,
-      end: (match.index || 0) + match[0].length
-    });
+function findPositionToInsertShim(input: string, pattern: RegExp) {
+  let lastImport;
+  // mimicking behavior of `String.matchAll` as it returns an iterator, not an array
+  for (const match of matchAllPolyfill(input, pattern)) {
+    lastImport = match;
   }
-  return matches;
+  if (!lastImport) {
+    return 0;
+  }
+
+  return (lastImport.index || 0) + lastImport[0].length;
 }
 
 export function provideCJSSyntax(code: string): Output | null {
@@ -38,8 +41,7 @@ export function provideCJSSyntax(code: string): Output | null {
     return null;
   }
 
-  const lastESMImport = matchAll(ESMStaticImportRegex, code, { type: 'static' }).pop();
-  const indexToAppend = lastESMImport ? lastESMImport.end : 0;
+  const indexToAppend = findPositionToInsertShim(code, ESMStaticImportRegex);
   const s = new MagicString(code);
   s.appendRight(indexToAppend, ESMShim);
 
diff --git a/packages/esm-shim/test/fixtures/cjs-multiple-imports.js b/packages/esm-shim/test/fixtures/cjs-multiple-imports.js
new file mode 100644
index 000000000..4026ed793
--- /dev/null
+++ b/packages/esm-shim/test/fixtures/cjs-multiple-imports.js
@@ -0,0 +1,10 @@
+import { constants } from 'node:crypto';
+
+import MagicString from 'magic-string';
+
+const child = require('child');
+
+const s = new MagicString('');
+const c = constants.SEP;
+
+export { child, s, c };
diff --git a/packages/esm-shim/test/fixtures/cjs-single-import.js b/packages/esm-shim/test/fixtures/cjs-single-import.js
new file mode 100644
index 000000000..a66296f07
--- /dev/null
+++ b/packages/esm-shim/test/fixtures/cjs-single-import.js
@@ -0,0 +1,7 @@
+import MagicString from 'magic-string';
+
+const child = require('child');
+
+const s = new MagicString('');
+
+export { child, s };
diff --git a/packages/esm-shim/test/snapshots/test.js.md b/packages/esm-shim/test/snapshots/test.js.md
index 2541760b5..e0176a0cb 100644
--- a/packages/esm-shim/test/snapshots/test.js.md
+++ b/packages/esm-shim/test/snapshots/test.js.md
@@ -49,3 +49,47 @@ Generated by [AVA](https://avajs.dev).
     ␊
     exports.child = child;␊
     `
+
+## inject cjs shim for esm output with a single import statement
+
+> Snapshot 1
+
+    `import MagicString from 'magic-string';␊
+    ␊
+    ␊
+    // -- Shims --␊
+    import cjsUrl from 'url';␊
+    import cjsPath from 'path';␊
+    import cjsModule from 'module';␊
+    const __filename = cjsUrl.fileURLToPath(import.meta.url);␊
+    const __dirname = cjsPath.dirname(__filename);␊
+    const require = cjsModule.createRequire(import.meta.url);␊
+    const child = require('child');␊
+    ␊
+    const s = new MagicString('');␊
+    ␊
+    export { child, s };␊
+    `
+
+## inject cjs shim for esm output with multiple import statements
+
+> Snapshot 1
+
+    `import { constants } from 'node:crypto';␊
+    import MagicString from 'magic-string';␊
+    ␊
+    ␊
+    // -- Shims --␊
+    import cjsUrl from 'url';␊
+    import cjsPath from 'path';␊
+    import cjsModule from 'module';␊
+    const __filename = cjsUrl.fileURLToPath(import.meta.url);␊
+    const __dirname = cjsPath.dirname(__filename);␊
+    const require = cjsModule.createRequire(import.meta.url);␊
+    const child = require('child');␊
+    ␊
+    const s = new MagicString('');␊
+    const c = constants.SEP;␊
+    ␊
+    export { c, child, s };␊
+    `
diff --git a/packages/esm-shim/test/snapshots/test.js.snap b/packages/esm-shim/test/snapshots/test.js.snap
index 2a0c38554..5143ca0dc 100644
Binary files a/packages/esm-shim/test/snapshots/test.js.snap and b/packages/esm-shim/test/snapshots/test.js.snap differ
diff --git a/packages/esm-shim/test/test.js b/packages/esm-shim/test/test.js
index 4419fa90f..3f9e5f8e4 100644
--- a/packages/esm-shim/test/test.js
+++ b/packages/esm-shim/test/test.js
@@ -41,3 +41,29 @@ test.serial('not inject cjs shim for cjs output', async (t) => {
   t.snapshot(output.code);
   t.falsy(output.map);
 });
+
+test.serial('inject cjs shim for esm output with a single import statement', async (t) => {
+  const bundle = await rollup({
+    input: 'test/fixtures/cjs-single-import.js',
+    plugins: [esmShim()],
+    external: ['magic-string']
+  });
+  const result = await bundle.generate({ format: 'es' });
+  t.is(result.output.length, 1);
+  const [output] = result.output;
+  t.snapshot(output.code);
+  t.falsy(output.map);
+});
+
+test.serial('inject cjs shim for esm output with multiple import statements', async (t) => {
+  const bundle = await rollup({
+    input: 'test/fixtures/cjs-multiple-imports.js',
+    plugins: [esmShim()],
+    external: ['magic-string', 'node:crypto']
+  });
+  const result = await bundle.generate({ format: 'es' });
+  t.is(result.output.length, 1);
+  const [output] = result.output;
+  t.snapshot(output.code);
+  t.falsy(output.map);
+});